Patent GB-371822-A (GB)
Title: Improvements in the manufacture and production of wetting, cleansing, emulsifying andthe like agents
IPC: C09G1/08
Filed: 1931-01-26
Abstract: Products useful as emulsifying agents are obtained by sulphonating derivatives of the hydrocarbon mixture corresponding to crude montanic acid.  The sulphonation of crude montan wax as such is excluded, but the derivatives which may be sulphonated include (1) carboxylic acids obtainable from crude, deresinified or otherwise pretreated montan wax by wet bleaching with oxidizing solutions or by distillation; (2) chlorination products of these carboxylic acids, obtainable by chlorinating the acids in a fused state or in solution in carbon tetrachloride or carbon bisulphide; (3) oxycarboxylic acids obtainable from the chlorinated acids by treatment with aqueous alkalis; (4) esters of the acids mentioned under (1) and (3) with aliphatic or aralkyl alcohols; (5) amides of the acids mentioned under (1) and (3), obtainable by treating the acids or their halides or esters with ammonia or liquid ammonia or amines such as methyl-, ethyl-, butyl-, hexyl-, cyclohexyl- and naphthylamines, aniline or toluidine; (6) alcohols obtainable by reduction from the acids mentioned under (1) and (3) or from their esters; (7) amines obtainable by converting the alcohols mentioned under (6) into halides, and treating these with ammonia or primary or secondary amines; (8) unsaturated compounds prepared by splitting off water from the oxycarboxylic acids mentioned under (3), or hydrogen chloride from the chlorine derivatives mentioned under (2); (9) aminoacids obtainable by treating the chlorinated acids mentioned under (2) with ammonia; (10) chlorination products of the alcohols mentioned under (6); (11) aminoalcohols obtained by treating the chlorinated alcohols mentioned under (10) with ammonia or amines. The derivatives may be sulphonated in admixture with each other or with other organic substances capable of being sulphonated, such as olefines, alcohols, and carboxylic acids and amides, preferably containing at least eight carbon atoms.  The products may be used in conjunction with other substances such as soaps, turkey red oils, aromatic sulphonic acids, salts such as perborates and Glauber's salt, protective colloids such as glue, gelatin, and gum arabic, and organic solvents such as cyclohexanol and other alcohols, cyclohexanone and other ketones, benzine, benzene, and trichlorethylene.  They may be applied in the textile, leather, and paper industries, and in the manufacture of drilling and lubricating preparations and polishes.  According to the examples, (1) montan wax, bleached as described in Specification 305,552, [Class 2 (iii), Dyes &c.], is chlorinated, and the product is heated with aqueous caustic potash and acidified ; the isolated oily product is added to an ethereal solution of chlorsulphonic acid, and the sulphonated product worked up; (2) montanwax, bleached as described in Specification 305,552, is heated under pressure with liquid ammonia and the amides so obtained are heated with chlorsulphonic acid in pyridine solution, yielding sulphamic acids; (3) fatty acids obtained by distilling crude montan wax are subjected to catalytic hydrogenation, and the mixture of alcohols so obtained is treated in ether with chlorsulphonic acid; (4) deresinified montan wax is re-esterified with ethyl alcohol, and the product is hydrogenated under pressure in the presence of nickel; the mixture of alcohols so obtained is treated with sulphuric acid in the presence of acetic anhydride; the product may be used as an ethanolamine salt; (5) a mixture of alcohols, obtained as in example (3), is treated with thionyl chloride, and the product is treated with concentrated ammonia solution; the mixture of primary, secondary, and tertiary amines so obtained is sulphonated as in example (3); (6) the acids obtained by saponifying bleached montan wax are esterified with benzyl alcohol, and the esters are treated in trichlorethylene solution with chlorsulphonic acid; (7) the acids obtained by distilling montan wax are esterified with ethylene glycol monocresyl ether, and the esters are sulphonated as described in example (6). Specifications 19502/90, [Class 2, Acids and salts, Organic &c.], 303,281, 309,042 (as open to inspection under Sect. 91 (3) (a)), [both in Class 2 (iii), Dyes &c.], and 360,493 also are referred to.ALSO:Products useful as wetting, emulsifying, cleansing and sizing agents are obtained by sulphonating derivatives of the hydrocarbon mixture corresponding to crude montanic acid.  The sulphonation of crude montan wax as such is excluded, but the derivatives which may be sulphonated include (1) carboxylic acids obtainable from crude, deresinified or otherwise pretreated montan wax by wet bleaching with oxidizing solutions or by distillation; (2) chlorination products of these carboxylic acids, obtainable by chlorinating the acids in a fused state or in solution in carbon tetrachloride or carbon bisulphide; (3) oxycarboxylic acids obtainable from the chlorinated acids by treatment with aqueous alkalies; (4) esters of the acids mentioned under (1) and (3) with aliphatic or aralkyl alcohols; (5) amides of the acids mentioned under (1) and (3), obtainable by treating the acids or their halides or esters with ammonia or liquid ammonia or amines such as methyl-, ethyl-, butyl-, hexyl-, cyclohexyl- and naphthylamines, aniline or toluidine; (6) alcohols obtainable by reduction from the acid mentioned under (1) and (3) or from their esters; (7) amines obtainable by converting the alcohols mentioned under (6) into halides and treating these with ammonia or primary or secondary amines; (8) unsaturated compounds prepared by splitting off water from the oxycarboxylic acids mentioned under (3), or hydrogen chloride from the chlorine derivatives mentioned under (2); (9) aminoacids obtainable by treating the chlorinated acids mentioned under (2) with ammonia; (10) chlorination products of the alcohols mentioned under (6); (11) aminoalcohols obtained by treating the chlorinated alcohols mentioned under (10) with ammonia or amines. The derivatives may be sulphonated in admixture with each other or with other organic substances capable of being sulphonated, such as olefines, alcohols, and carboxylic acids and amides, preferably containing at least eight carbon atoms.  The sulphonation may be effected with concentrated sulphuric acid, oleum, chlorsulphonic acid, or sulphur trioxide in the presence or absence of diluents such as ether, chloroform, trichlorethylene, or nitrobenzene, and (or) of dehydrating agents such as phosphorus pentoxide, acetic anhydride or acetyl chloride, and (or) of surface catalysts such as active carbon. The sulphonation temperature may lie between -- 10 and 120 DEG  C. The products may be used in conjunction with other substances such as soaps, turkey red oils, aromatic sulphonic acids, salts such as perborates and Glauber's salt, protective colloids such as glue, gelatin and gum arabic, and organic solvents such as cyclohexanol and other alcohols, cyclohexanone and other ketones, benzine, benzene and trichlorethylene.  They may be applied in the textile, leather and paper industries, and in the manufacture of drilling and lubricating preparations and polishes.  According to the examples, (1) montan wax, bleached as described in Specification 305,552, [Class 2 (iii), Dyes &c.], is chlorinated, and the product is heated with aqueous caustic potash and acidified; the isolated oily product is added to an ethereal solution of chlorsulphonic acid, and the sulphonated product worked up; (2) montan wax, bleached as described in Specification 305,552, is heated under pressure with liquid ammonia, and the amides so obtained are heated with chlorsulphonic acid in pyridine solution, yielding sulphamic acids; (3) fatty acids obtained by distilling crude montan wax are subjected to catalytic hydrogenation, and the mixture of alcohols so obtained is treated in ether with chlorsulphonic acid; (4) deresinified montan wax is re-esterified with ethyl alcohol, and the product is hydrogenated under pressure in the presence of nickel; the mixture of alcohols so obtained is treated with sulphuric acid in the presence of acetic anhydride; the product may be used as an ethanolamine salt; (5) a mixture of alcohols, obtained as in example (3), is treated with thionyl chloride, and the product is treated with concentrated ammonia solution; the mixture of primary, secondary and tertiary amines so obtained is sulphonated as in example (3); (6) the acids obtained by saponifying bleached montan wax are esterified with benzyl alcohol and the esters are treated in trichlorethylene solution with chlorsulphonic acid; (7) the acids obtained by distilling montan wax are esterified with ethylene glycol monocresyl ether, and the esters are sulphonated as described in example (1). Specifications 19502/90, [Class 2, Acids and salts, Organic &c.], 303,281, 309,042, [both in Class 2 (iii), Dyes &c.], and 360,493 also are referred to.ALSO:Products useful as sizes are obtained by sulphonating derivatives of the hydrocarbon mixture corresponding to crude montanic acid.  The sulphonation of crude montan wax as such is excluded, but the derivatives which may be sulphonated include (1) carboxylic acids obtainable from crude, deresinfied or otherwise pretreated montan wax by wet bleaching with oxidizing solutions or by distillation; (2) chlorination products of these carboxylic acids, obtainable by chlorinating the acids in a fused state or in solution in carbon tetrachloride or carbon bisulphide; (3) oxycarboxylic acids obtainable from the chlorinated acids by treatment with aqueous alkalies; (4) esters of the acids mentioned under (1) and (3) with aliphatic or aralkyl alcohols; (5) amides of the acids mentioned under (1) and (3), obtainable by treating the acids or their halides or esters with ammonia or liquid ammonia or amines such as methyl-, ethyl-, butyl-, hexyl-, cyclohexyl- and naphthylamines